Sodium Hydroxide → HCID 178478633, compound

HRID 1581136Notes

Reaction equation

HRID 1581136 reaction equation
[ClH:1].Cl.[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1N.[C:12]([NH:14][C:15]([NH2:17])=[NH:16])#[N:13].[OH-].[Na+]>O>[ClH:1].[ClH:1].[NH:14]([C:12]1[N:4]([CH3:3])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:13]=1)[C:15]([NH2:17])=[NH:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 91296N-Methyl-o-phenylenediamine dihydrochlorideHCID 178418324HCID 178418324, compound

Product 1

HCID 178478633HCID 178478633, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-methyl-o-phenylenediamine dihydrochloride (10.80g. 0.005 mol) and cyanoguanidine (9.30g, 0.11 mol) was heated under reflux in water (80 ml) for 21/2 hours. The reaction mixture was cooled, basified with excess 40% sodium hydroxide, and the resulting precipitate filtered, washed with water and dried in vacuo. (7.19g; m.p. 142°-146°C). This was dissolved in excess dilute hydrochloric acid and evaporated in vacuo. The crude hydrochloride was recrystallised from ethanol/ether to yield 2-guanidino-1-methylbenzimidazole dihydrochloride (600g; 42%) as off-white micro-crystals m.p. 228°-238°C.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customdried in vacuo
  6. dissolutionThis was dissolved in excess dilute hydrochloric acid
  7. customevaporated in vacuo
  8. customThe crude hydrochloride was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-232650ec2c38446eacf20160de375e03
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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